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04259

Sigma-Aldrich

N-Ethylmaleimide

BioUltra, ≥99.0% (HPLC)

Synonym(s):

NEM

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About This Item

Empirical Formula (Hill Notation):
C6H7NO2
CAS Number:
128-53-0
Molecular Weight:
125.13
Beilstein/REAXYS Number:
112448
EC Number:
204-892-4
MDL number:
MFCD00005509
UNSPSC Code:
12352106
PubChem Substance ID:
329747899
NACRES:
NA.26

product line

BioUltra

Quality Level

200

assay

≥99.0% (HPLC)

impurities

insoluble matter, passes filter test

ign. residue

≤0.05%

bp

210 °C (lit.)

mp

43-46 °C (lit.)
44-47 °C

solubility

methanol: 1 M at 20 °C, clear, colorless

anion traces

chloride (Cl-): ≤50 mg/kg
sulfate (SO42-): ≤100 mg/kg

cation traces

Al: ≤5 mg/kg
Ba: ≤5 mg/kg
Bi: ≤5 mg/kg
Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Li: ≤5 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Mo: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Sr: ≤5 mg/kg
Zn: ≤5 mg/kg

absorption

cut-off at 382 nm in methanol at 1 M

storage temp.

2-8°C

SMILES string

CCN1C(=O)C=CC1=O

InChI

1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3

InChI key

HDFGOPSGAURCEO-UHFFFAOYSA-N

Gene Information

human ... SLC6A3(6531) , SLC6A4(6532)

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Application

N-Ethylmaleimide (NEM) has been used:
  • to prepare NEM-modified myosin beads
  • to block unmodified free thiols in samples
  • as a supplement in IP lysis/wash buffer for in vitro SUMOylation assay

Reagent for the covalent modification of cysteine residues in proteins.

Biochem/physiol Actions

Augments currents from native M-channels in sympathetic neurons and acts as an opener for KCNQ2, KCNQ4 and KCNQ5 channels.
Sulfhydryl alkylating agent that inactivates NADP-dependent isocitrate dehydrogenase and many endonucleases.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

163.2 °F - closed cup

flash_point_c

72.9 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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SUMOylation of periplakin is critical for efficient reorganization of keratin filament network
Gujrati M, et al.
Molecular Biology of the Cell, 30(3), 357-369 (2019)
Measuring the kinetic and mechanical properties of non-processive myosins using optical tweezers
Greenberg MJ, et al.
Methods in Molecular Biology, 483-509 (2017)
Resin-assisted enrichment of thiols as a general strategy for proteomic profiling of cysteine-based reversible modifications
Jia Guo
Nature Protocols, 9(1), 64-75 (2014)
Bon-Kyoung Koo et al.
Nature, 488(7413), 665-669 (2012-08-17)
LGR5+ stem cells reside at crypt bottoms, intermingled with Paneth cells that provide Wnt, Notch and epidermal growth factor signals. Here we find that the related RNF43 and ZNRF3 transmembrane E3 ubiquitin ligases are uniquely expressed in LGR5+ stem cells.
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Plant physiology, 161(1), 508-520 (2012-11-16)
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